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D141

Sigma-Aldrich

Digitonin

Used as non-ionic detergent

Synonym(s):

Digitin

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100 MG
€109.00
500 MG
€376.00

€109.00

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100 MG
€109.00
500 MG
€376.00

About This Item

Empirical Formula (Hill Notation):
C56H92O29
CAS Number:
11024-24-1
Molecular Weight:
1229.31
Beilstein:
78654
EC Number:
234-255-6
MDL number:
MFCD00077729
UNSPSC Code:
12161900
PubChem Substance ID:
24893429
NACRES:
NA.25

€109.00

Please contact Customer Service for Availability
Request a Bulk Order

biological source

plant seeds (Digitalis purpurea)

Quality Level

200

form

powder

optical activity

[α]20/D −54°, c = 2.8 in methanol(lit.)

mol wt

micellar avg mol wt 70,000

aggregation number

60

impurities

<6.0% water

CMC

<0.5 mM (20-25°C)
<0.5 mM (20-25°C)

mp

230-240 °C (dec.) (lit.)

solubility

H2O: ~5 % (w/v) (solubilized by heating to 95 °C - 98 °C and then cooling to room temp.)

SMILES string

C[C@@]12[C@]([C@@H]3C)([H])[C@](O[C@]34CC[C@@H](C)CO4)([H])[C@@H](O)[C@@]1([H])[C@@](CC[C@]5([H])[C@@]6(C[C@@H](O)[C@H](O[C@]([C@@H]([C@@H](O)[C@H]7O[C@@](O[C@H](CO)[C@@H](O)[C@@H]8O[C@@](OC[C@@H](O)[C@@H]9O)([H])[C@@H]9O)([H])[C@@H]8O[C@@](O[C@H](CO)[C@H

InChI

1S/C56H92O29/c1-19-7-10-56(75-17-19)20(2)31-45(85-56)37(67)32-22-6-5-21-11-26(24(61)12-55(21,4)23(22)8-9-54(31,32)3)76-50-42(72)39(69)44(30(16-60)80-50)81-53-48(47(36(66)29(15-59)79-53)83-49-40(70)33(63)25(62)18-74-49)84-52-43(73)46(35(65)28(14-58)78-52)82-51-41(71)38(68)34(64)27(13-57)77-51/h19-53,57-73H,5-18H2,1-4H3/t19-,20+,21+,22-,23+,24-,25-,26-,27-,28-,29-,30-,31+,32-,33+,34-,35+,36-,37+,38+,39-,40-,41-,42-,43-,44+,45-,46+,47+,48-,49+,50-,51+,52+,53+,54-,55+,56-/m1/s1

InChI key

UVYVLBIGDKGWPX-KUAJCENISA-N

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General description

Digitonin, a steroidal saponin extracted from the purple foxglove plant (Digitalis purpurea), stands as a versatile non-ionic detergent crucial for cell biology and biochemical research. Its unique attributes position it as a valuable asset in the exploration of cellular membranes, membrane proteins, and intracellular components. Digitonin′s key properties and applications include its ability to solubilize membrane-bound proteins effectively while preserving their native conformation, making it an ideal tool for studying membrane protein interactions and activities.

Moreover, Digitonin selectively permeabilizes the cholesterol-rich plasma membrane, leaving organelle membranes intact. This feature facilitates the extraction and purification of specific organelles, contributing to the study of their functions and roles in cellular processes. The detergent′s capability to permeabilize diverse cell types allows the study of intracellular components and processes by introducing molecules, antibodies, or enzymes into cells. Additionally, Digitonin finds application in immunocytochemistry experiments, enabling the labeling and detection of intracellular proteins and structures.

Application

Digitonin has been used along with permeabilization buffer for cyclic guanosine monophosphate-adenosine monophosphate (cyclic GMP-AMP) stimulation in cells.
Digitonin has been used in a study to assess a procedure for isolating mitochondria from ascites tumor cells. [1] It has also been used in a study to investigate its effect on the cytotoxicity of plant secondary metabolites in cancer cells. [2]

Biochem/physiol Actions

Digitonin plays a key role in permeabilizing cell membranes. It is capable of lysing eukaryotic cells but not bacterial membranes. It is also used to solubilize membrane components. It helps to create pores by interacting specifically with cholesterol in the membrane. It is preferred in biotechnology due to its mild detergency. This membrane-active compound act with doxorubicin against multi-drug resistant cancer cells.

Features and Benefits

Highly versatile compound for your cell biology and biochemical research

Quality

Preparation is free of water-insoluble constituents.

Other Notes

For additional information on our range of Biochemicals, please complete this form.

comparable product

Product No.
Description
Pricing

D5628

Digitonin, ~50% (TLC)

Pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

Signal Word

Danger

Hazard Statements

H301,H373

Precautionary Statements

P301 + P310 + P330 - P314

Hazard Classifications

Acute Tox. 3 Oral - STOT RE 2

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCM7280
BCCM2254
BCCH6132
BCCH7960
BCCH3017

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Spermidine BioReagent, for molecular biology, suitable for cell culture, &#8805;98%

Sigma-Aldrich

S0266

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Saponin A glycoside used to permeabilize cellular membranes. Exhibits hemolytic activity.

Millipore

558255

Saponin

IGEPAL&#174; CA-630 for molecular biology

Sigma-Aldrich

I8896

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R W Moreadith et al.
Analytical biochemistry, 137(2), 360-367 (1984-03-01)
A new, improved procedure for isolating mitochondria from ascites tumor cells is described. The unique feature of this technique is the use of digitonin to make the cells susceptible to disruption by Teflon pestle/glass vessel homogenization. The yield and respiratory
Dominic S Alonzi et al.
Cellular and molecular life sciences : CMLS, 70(15), 2799-2814 (2013-03-19)
Endoplasmic reticulum-associated degradation (ERAD) is a key cellular process whereby misfolded proteins are removed from the endoplasmic reticulum (ER) for subsequent degradation by the ubiquitin/proteasome system. In the present work, analysis of the released, free oligosaccharides (FOS) derived from all
Wattamon Srisakuldee et al.
Cardiovascular research, 103(1), 72-80 (2014-03-22)
Fibroblast growth factor 2 (FGF-2) protects the heart from ischaemia- and reperfusion-induced cell death by a mechanism linked to protein kinase C (PKC)ε-mediated connexin 43 (Cx43) phosphorylation. Cx43 localizes predominantly to gap junctions, but has also been detected at subsarcolemmal
Xianying A Cui et al.
Journal of visualized experiments : JoVE, (70)(70), e50066-e50066 (2012-12-29)
In eukaryotes, most of the messenger RNAs (mRNAs) that encode secreted and membrane proteins are localized to the surface of the endoplasmic reticulum (ER). However, the visualization of these mRNAs can be challenging. This is especially true when only a
Xianying A Cui et al.
PLoS biology, 10(5), e1001336-e1001336 (2012-06-09)
In metazoans, the majority of mRNAs coding for secreted and membrane-bound proteins are translated on the surface of the endoplasmic reticulum (ER). Although the targeting of these transcripts to the surface of the ER can be mediated by the translation
View All Related Papers

Protocols

Solubilization of Membrane Proteins

This page shows how to solubilize membrane proteins with products from Cytiva.

Questions

1–9 of 9 Questions  

  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

      Helpful?

  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

      Helpful?

  3. What is the stability of D141 and N7537 in the stock solution in DMSO?

    1 answer

    1. D141 can remain stable for up to one week when refrigerated, whether in water or DMSO. On the other hand, N7537 can be stored in DMSO (or ethanol) at -20°C for up to two weeks.

      Helpful?

  4. Wie kann ich das Produkt vor den Experiment aufreinigen? haben Sie ein Protokoll dazu? danke Beste Grüße Ayoub

    1 answer

    1. There is no specific protocol for the purification of item D141 available. The quality of this product is already detailed as being free of water-insoluble constituents. The purpose of the purification would be to remove these water-insoluble impurities.
      This is usually done through a recrystallization technique. This product will dissolve at 1 g in 20 mL of water at 95 - 98°C, as detailed on the corresponding specification sheet:
      https://www.sigmaaldrich.com/specification-sheet/SIGMA/D141

      Thus, it should be dissolved directly in water with high heat without any prior purification.

      Helpful?

  5. What is the storage condition for digitonin ?

    1 answer

    1. This product should be stored in room temperature. Please keep the container tightly closed in a dry and well-ventilated place. To view safety handling information, please view the safety data sheet for the product:
      https://www.sigmaaldrich.com/sds/sigma/d141

      Helpful?

  6. What is the Department of Transportation shipping information for this product?

    1 answer

    1. Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product.

      Helpful?

  7. What is the solution stability of Product D141, Digitonin?

    1 answer

    1. We recommend making solutions fresh for use.

      Helpful?

  8. What is the solubility of Product D141, Digitonin?

    1 answer

    1. The solubility of D141 is tested by heating a 5% solution in water to 95-98°C and then cooling the solution to room temperature. After cooling, the solution should remain practically clear for at least 24 hours. The product can also be dissolved at 100mg/4mL of warm ethanol.

      Helpful?

  9. How pure is Product D141, Digitonin?

    1 answer

    1. The purity of this product is evaluated by Thin Layer Chromatography. The actual results are lot specific and will be reported on the Certificate of Analysis of each lot.

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